DEUTERIUM-ENRICHED LISDEXAMFETAMINE
The present application describes deuterium-enriched lisdexamfetamine, pharmaceutically acceptable salt forms thereof, and methods of treating using the same.
1 . A deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 25 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 25 is at least 4%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 25 is selected from at least 4%, at least 6%, at least 14%, at least 19%, at least 26%, at least 32%, at least 39%, at least 45%, at least 52%, at least 58%, at least 65%, at least 71%, at least 77%, at least 84%, at least 90%, at least 97%, and 100%.
3 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 5 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
4 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 6 -R 14 is selected from at least 11%, at least 22%, at least 33%, at least 44%, at least 56%, at least 67%, at least 78%, 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 15 -R 20 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 21 -R 25 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
7 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-5 of Table 1.
8 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 6-10 of Table 2.
9 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 25 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 25 is at least 4%.
10 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 1 -R 25 is selected from at least 4%, at least 6%, at least 14%, at least 19%, at least 26%, at least 32%, at least 39%, at least 45%, at least 52%, at least 58%, at least 65%, at least 71%, at least 77%, at least 84%, at least 90%, at least 97%, and 100%.
11 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 1 -R 5 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
12 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 6 -R 14 is selected from at least 11%, at least 22%, at least 33%, at least 44%, at least 56%, at least 67%, at least 78%, 100%.
13 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 15 -R 20 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
14 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 21 -R 25 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
15 . An isolated deuterium-enriched compound of claim 9 , wherein the compound is selected from compounds 1-5 of Table 1.
16 . An isolated deuterium-enriched compound of claim 9 , wherein the compound is selected from compounds 6-10 of Table 2.
17 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 25 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 25 is at least 4%.
18 . A mixture of deuterium-enriched compound of claim 17 , wherein the compound is selected from compounds 1-5 of Table 1.
19 . A mixture of deuterium-enriched compound of claim 17 , wherein the compound is selected from compounds 6-10 of Table 2.
20 . A pharmaceutical composition, comprising: a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt form thereof.
21 . A method for treating attention-deficit hyperactivity disorder comprising:
administering, to a patient in need thereof, a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt form thereof.